Tom Simson is a "guileless youth," a young man whose name can be interpreted as the son of a simple man. He does not realize the severity of the predicament in which the outcasts are placed, and he gladly joins the others, thinking that there is safety in numbers. More importantly, Tom has met up with John Oakhurst before. Oakhurst had won all of Tom's money--$40--in a card game, but Oakhurst, ever the happy-go-lucky and kind gentleman, returned Tom's money to him.

After the game was finished, Mr. Oakhurst drew the youthful speculator behind the door and thus addressed him: “Tommy, you're a good little man, but you can't gamble worth a cent. Don't try it over again.” He then handed him his money back, pushed him gently from the room, and so made a devoted slave of Tom Simson.

Tom has not forgotten Oakhurst's kindness, and he is more than willing to trust the gambler with his life and that of his young love, Piney Woods.